Sodium Hydroxide → HCID 72448489, compound

HRID 1623164Notes

Reaction equation

HRID 1623164 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:21])[N:14]([CH2:15][CH2:16][CH2:17][C:18](=O)[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[NH2:23][OH:24].[OH-].[Na+]>C(O)C.O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:21])[N:14]([CH2:15][CH2:16][CH2:17][C:18](=[N:23][OH:24])[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 58837346HCID 58837346, compound

Product 1

HCID 72448489HCID 72448489, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 5-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one, 2.20 g, 7.80 mmol) in ethanol (50 mL) was heated at reflux, and a solution of hydroxylamine hydochloride (1.08 g, 15.6 mmol) in water (10 mL) was added, followed by a solution of sodium hydroxide (0.94 g, 23.5 mmol) in water (10 mL). After 30 minutes, the reaction mixture was cooled in an ice bath to cause crystallization of the product, which was isolated by filtration and recrystallized from aqueous DMSO to provide 5-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one oxime in about a 16 to 1 mixture of E and Z isomers as yellow crystals, mp 264-266° C.

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled in an ice bath
  3. customcrystallization of the product
  4. customwhich was isolated by filtration
  5. customrecrystallized from aqueous DMSO

Sources & evidence

ORD record
ord-9a2f03fb8bfe438584a5015f7d821958
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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